1,4-Naphthalenedione, 2-chloro-3-methyl- → 1,4-Naphthoquinone, 2-methoxy-3-methyl-

HRID 1535018Notes

Reaction equation

HRID 1535018 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[CH3:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:15][O-:16].[Na+]>O1CCCC1>[CH3:15][O:16][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[CH3:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 1233681,4-Naphthalenedione, 2-chloro-3-methyl-HCID 10942334Sodium Methoxide

Product 1

HCID 794411,4-Naphthoquinone, 2-methoxy-3-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chloro-3-methyl-1,4-naphthoquinone (10.3 g) in tetrahydrofuran (100 mL) was treated dropwise with a solution of sodium methoxide (320 g) in tetrahydrofuran (25 mL) at room temperature. After stirring overnight, the mixture was evaporated, and the residue was taken up in ether. The organic layer was washed with brine, dried, filtered and evaporated. Chromatography over silica gel gave 2-methoxy-3methyl-1,4-naphthoquinone, m.p. 93°-94° C.

Workup

  1. customthe mixture was evaporated
  2. washThe organic layer was washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-245096c3d16e4c5696a6254962d021c6
Source dataset
uspto-grants-1992_02
Patent number
US05091558

Reaction notes

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